Today, we have the great pleasure in bringing you an interview we conducted with Jason Calacanis. For those of you who don’t know about him, Jason is a very successful angel investor and the creator of some of the Internet’s most valuable websites. Interview by namepros forums (NP).

Some of @jason calacanis’s achievements include creating the website Mahalo.com, co-founding Weblogs Inc, and most recently creating the LAUNCH festival, an annual event with an average of 10,000 attendees.

Jason has made many notable investments as an angel investor in companies such as Tumblr, Uber, and Evernote. He also happens to be the owner of one of the most sought after domain names on the Internet: 20.com.

Having acquired the domain name in 2006, Jason can now expect to sell this asset for a multiple seven-figure sum. In the interview below, we ask Jason a number of questions related to domain names, 20.com, new gTLDs, and his advice for startups in relation to domain names.

NP: What drove you to buy 20.com for $75k in 2006? Was it for a specific company or did you see intrinsic value in it?

Jason: I wanted to start a Wikipedia-like search engine, where consumers would rank the top 10 or 20 links. My thinking was, well, you’re never going to need more than 20 links about a topic. I had also bought kokua.com and mahalo.com at the same time; after testing the names with people, I found everyone loved Mahalo.com.

NP: We’ve noticed that over the years you’ve received increasingly larger offers for 20.com. Were you ever tempted to sell the name at a lower price, considering your original acquisition fee?

Jason: I’ve been super busy angel investing and never considered what it was worth. Given that I’m getting 20 emails a week, I think it’s time for me to let someone use it. It’s kind of a waste to let these premium domains sit and collect dust in my mind.

NP: Would you consider yourself to be a domain investor? Do you plan to make more domain purchases after selling 20.com?

Jason: No, I’m not a domainer, I’m an angel investor. I run launch.co, which includes an incubator, conferences and my angel fund. Domains are awesome assets for startups, but startups are driven by founders — so I chase the founders, not the domains.

NP: What is the most expensive domain you’ve ever purchased? Can you share the domain name and/or the price that was paid?

Jason: Tied: Inside.com and 20.com, around the same price (and same value today I would bet).

NP: What’s your favorite domain that you own?

Jason: Kokua.com, Loaa.com or ADAY.com.

NP: What was the first domain you ever purchased?

Jason: Can’t remember!

NP: What level of importance do you place on a domain in your marketing stack?

Jason: It’s awesome if a startup can own a premium domain — eventually. You don’t need it from day one. Eventually, if your business succeeds, it’s a great checkbox to own Uber.com or Calm.com.

NP: What do you think about the new gTLDs such as .club, .tech, .technology, .xyz? Would you recommend that startups use them?

Jason: I think these domains are great for starting out, but eventually you need to get the .com version of your name. Ironically, the more gTLDs they create, the more valuable the .coms become. It’s like a bunch of cities popping up around Manhattan: as they go up in value, the city in the center goes supernova.

NP: Do you advise startups on domain name acquisitions? If so, can you share some of your common recommendations?

Jason: I do this often, and the conversation is usually “fake it until you make it.” So, there is no problem being TeslaMotors.com forever. Obviously the car and people who make the car are the most important aspect of the success of that company.

However, if the person with Tesla.com decides they want to buy a nice condo or house, sure, it’s a great idea to spend $500k or $1m buying that name. If the person with Tesla.com waits too long, they miss the opportunity to take 10% of the purchase price in stock (or some kicker like that). They also risk pissing off the management team at a startup, who will eventually realize, “well, our cars are the best in the world and this domain name is not essential.”

–

Thanks to Jason for taking the time out of his very busy schedule to take part in this interview.